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Date: Thu, 23 Apr 2020 17:32:15 +0300
From: PromiseLabs Pentest Research <>
Subject: Re: spoofing of local email sender via a homoglyph


To follow up on your questions:

1) How exactly would a mail server block a message from an existing
username (even without the homoglyph attack for now), and under what
scenario - message being submitted locally or via SMTP?

The current configuration actually blocks any non-authorized requests as 
explained in the description. The use-case of this (from my perspective) 
is that it could be used to advance a social-engineer attack into 
tricking the recipients believing that they are getting an email from a 
high-level position at the company.

It's related to the from header.

Issuing a regular unauthenticated request, trying to send an email from 
john.doe, which is a high-level user at the company:
$ nc -v *** OMITTED *** 25
Connection to *** OMITTED *** 25 port [tcp/smtp] succeeded!
220 *** OMITTED *** ESMTP Postfix
mail from:
250 2.1.0 Ok
rcpt to:
553 5.7.1 <>: Sender address rejected: not logged in

As you can see, the mail server rejects the request as the existing user 
hasn't authenticated himself.

However, issuing a request using a homoglyph character:
$ echo -ne "j\xce\" | xclip -selection clipboard
$ nc -v *** OMITTED ***  25
Connection to *** OMITTED ***  25 port [tcp/smtp] succeeded!
220 *** OMITTED ***  ESMTP Postfix
mail from: jο
250 2.1.0 Ok
rcpt to:
250 2.1.5 Ok
354 End data with <CR><LF>.<CR><LF>

The victim would get an email thinking it's from the actual john.doe 

Whether this is applicable for assigning a CVE it's up to you decide, 
the only actual risk here discovered so far is a social-engineering 

Plamen Dimitrov
Penetration Tester, CEH & OSCP certified

Promise Solutions LTD
Penetration Testing and Managed Security services
+359 883 22 05 12

On 2020-04-23 16:31, Solar Designer wrote:
> Hi,
> As list moderator, I took the liberty of changing the Subject of this
> posting to include the (claimed) vulnerability type, and not to single
> out the possibly irrelevant choice of software/version.  The original
> message Subject was:
> Subject: Fwd: Re: [scr882459] postfix 2.10.1 (other versions may be 
> affected)
> To make having this in here reasonable, I think we should first 
> consider
> discussing the general (non-)issue and only then specific software.
> Speaking mostly in general, not focusing on Postfix:
> On Thu, Apr 23, 2020 at 03:10:55PM +0300, PromiseLabs Pentest Research 
> wrote:
>> >> Postfix allows an email from unsanitized input, pretending to be from
>> >> an existing user on the mail system, which may look exactly the same.
>> >> For example, it is possible sending an email using the hex character
>> >> \xce\ xbf, which looks exactly like the letter 'o'. In case the user
>> >> john.doe exists on the mail server, postfix would not allow to send an
>> >> email from this email account unless an unauthorized attempt is made.
>> >> However, in case we substitute the letter 'o' with the hex character
>> >> \xce\xbf, it will look exactly like it's being sent from john.doe,
>> >> although john.doe (j<\xce\xbf)hn.doe) is actually different from
>> >> the other.
> How exactly would a mail server block a message from an existing
> username (even without the homoglyph attack for now), and under what
> scenario - message being submitted locally or via SMTP?
> For locally submitted messages, depending on mail server architecture,
> it may be technically possible to infer the real sender (e.g., which
> user invoked an SGID program to submit the message to the queue, or
> which user connected to a Unix domain socket).  However, if so the mail
> server would reasonably not merely block sending mail from other
> existing local usernames (and allow mail from non-existent 
> local-looking
> usernames) but would rather insist on the message having the one 
> correct
> username specified as its sender (retrieving the username by UID and
> either substituting it or comparing exact strings, so a homoglyph 
> attack
> is irrelevant).
> For messages received via SMTP, the exact sender can generally not be
> determined, but a message appearing to come from a locally hosted 
> domain
> name may be accepted or rejected or inbetween depending on anti-spam
> settings and such (which may also provide limited anti-spoofing).  I'd
> expect such configuration to be per-domain (applying regardless of
> whether the claimed sender's name exists locally or not), not per-user.
> While use cases can exist where it'd make sense to reject only messages
> from usernames that exist locally, that feels like a special case, and 
> I
> doubt is a default configuration - or is it a default somewhere?  Even
> if it is, is it an expected security feature (rather than a best-effort
> anti-spam filter, perhaps one of many)?  That's highly doubtful.
> Finally, are we talking about envelope-from, header From, header 
> Sender,
> or/and something else?
> With these questions, I am trying to show that PromiseLabs' report
> leaves so much unspecified that claiming a specific attack is 
> premature.
> Let alone request (and even successfully obtain) a CVE ID.
>> > Use CVE-2020-12063.
> So now we have a CVE ID specifically against Postfix while the issue is
> probably generic (or possibly a non-issue, depending on how you look at
> it) and if there's anything specific to Postfix here then it's possibly
> Postfix actually trying to prevent spoofing (or just spam) in some
> cases, but not doing so perfectly.  Should either of these cases really
> result in a CVE ID against Postfix?
> Also, is the issue (if one exists) potentially fixable?  Probably not
> directly - that is, there's probably no reliable way to prevent just 
> the
> homoglyph attacks.  Instead, either whatever check possibly exists can
> be removed or relaxed (also accept messages appearing from usernames
> that do exist locally) for the sake of consistency, or the check can be
> changed to be per-domain.  Either way, it'd not care about the 
> usernames
> anymore (assuming it currently somehow does).
> I suggest that PromiseLabs research and describe the issue for real,
> which in my opinion they did not yet.
> Alexander

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